In a recent candid discussion with Howard Stern, Bill Murray revealed a surprising regret from his prolific film career: he wishes he had worked with the legendary Clint Eastwood. Despite his long list of iconic roles, there’s one collaboration that still haunts him.

Reflecting on his decision, Murray recounted how he was captivated by Eastwood's films from that era, like “Thunderbolt and Lightfoot.” He noted the emotional depth afforded to Eastwood's sidekicks, which motivated him to reach out to the acclaimed director. “I thought, his sidekick gets killed, avenges him, but has an incredible death scene. I really wanted to be a part of something like that,” he noted.

Coming off the success of his 1981 hit comedy, "Stripes," Murray grew intrigued by a project Eastwood proposed—a military comedy. However, he had a lingering fear of being typecast into a specific genre. Murray recalled the moment he called Eastwood, saying, “He asked if I wanted to do another service comedy, and I panicked. I thought, ‘Would I become like Abbott and Costello? Is this the path for me?’ In that moment, I decided to decline the opportunity.”

Fast forward a few years, Eastwood went ahead to create the war film “Heartbreak Ridge,” which featured the Oscar-winning actor as Marine Gunnery Sergeant Tom Highway—a role that showcased Eastwood’s masterful blend of action and humor.

Murray expressed his regret saying, “It’s one of the few regrets I have. It was a big-scaled project and I think it would have been incredible. I don't know if I would have had a memorable death scene, but the comedic aspects of it would have been fantastic.” He emphasized that Eastwood had access to real military resources from World War II, which promised a production filled with prowess and excitement.

He also shared a humorous moment, noting, “Whenever I see Clint, I tell him, ‘I’m sorry, I wish I’d done that, Clint. I really am.’ But I know he’s over it. He’s a very resilient guy.”

In an interesting twist, Stern reminded listeners that “Stripes” was initially intended for the comedy duo, Cheech and Chong. Murray chimed in, suggesting that the film could have taken on a different vibe with them—full of stoner humor and antics.

Despite the paths taken and missed, Murray’s narrative reflects a deep appreciation for the artistry of filmmaking and the remarkable relationships formed throughout his career. As the years roll on, one can only wonder what other opportunities may have been lost in Hollywood’s labyrinth—a place filled with dreams, risks, and the occasional regret.